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【结 构 式】 
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【分子编号】63437 【品名】1-(4-methoxyphenyl)-2-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanone 【CA登记号】 |
【 分 子 式 】C22H26O4 【 分 子 量 】354.44604 【元素组成】C 74.55% H 7.39% O 18.06% |
合成路线1
该中间体在本合成路线中的序号：(XXII)Condensation of desoxybenzoin (I) with 2-(tetra-hydropyranyloxy)ethyl bromide (XIV) by means of aqueous NaOH and TEBAC as before gives 1,2-diphenyl-4-(tetrahydropyranyloxy)-1-butanone (XV), which by a Grignard condensation with 4-methoxyphenylmagnesium bromide (XVI) -prepared from 4-bromoanisole (XVII) and Mg in THF- provides the triphenylbutanol derivative (XVIII). Cleavage of the THP-protecting group of compound (XVIII) with H2SO4 in ethanol/water at room temperature affords the butane-1,4-diol derivative (XIX), which is cyclized by means of H2SO4 in hot ethanol/ water to yield 2-(4-methoxyphenyl)-2,3-diphenyltetrahydrofuran (XX). Finally, this compound is treated with 48% HBr in refluxing AcOH to give 4-(4-hydroxyphenyl)-3,4-diphenyl-3-buten-1-ol (X) as a (Z):(E)-isomeric mixture, from which the desired (Z)-isomer is separated by chemical work up.
| 【1】 Sorbera, L.A.; Castaner, J.; Bayes, M.; Ospemifene. Drugs Fut 2004, 29, 1, 38. |
| 【2】 Toivola, R.J.; Karjalainen, A.J.; Kurkela, K.O.A.; Soderwall, M.-L.; Kangas, L.V.M.; Blanco, G.L.; Sundquist, H.K. (Orion Corporation); Tri-phenyl alkene derivs. and their oestrogenic, anti-oestrogenic and progestanic uses. US 4996225; US 5491173 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 41003 | 1,2-diphenyl-1-ethanone; Deoxybenzoin-2-phenylacetophenone; Dexybenzoin | 451-40-1 | C14H12O | 详情 | 详情 |
| (X) | 52025 | 4-[(Z)-4-hydroxy-1,2-diphenyl-1-butenyl]phenol | C22H20O2 | 详情 | 详情 | |
| (XIV) | 26934 | 2-bromoethyl tetrahydro-2H-pyran-2-yl ether | C7H13BrO2 | 详情 | 详情 | |
| (XV) | 52021 | 1,2-diphenyl-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanone | C21H24O3 | 详情 | 详情 | |
| (XVI) | 37674 | Bromo(4-methoxyphenyl)magnesium; 4-Methoxyphenylmagnesium bromide | 352-13-6 | C7H7BrMgO | 详情 | 详情 |
| (XVII) | 63436 | 1-bromo-4-methoxybenzene; 4-bromophenyl methyl ether | C7H7BrO | 详情 | 详情 | |
| (XVIII) | 52022 | 1-(4-methoxyphenyl)-1,2-diphenyl-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol | C28H32O4 | 详情 | 详情 | |
| (XIX) | 52023 | 1-(4-methoxyphenyl)-1,2-diphenyl-1,4-butanediol | C23H24O3 | 详情 | 详情 | |
| (XX) | 52024 | 2-(4-methoxyphenyl)-2,3-diphenyltetrahydrofuran; 4-(2,3-diphenyltetrahydro-2-furanyl)phenyl methyl ether | C23H22O2 | 详情 | 详情 | |
| (XXI) | 30343 | 1-(4-methoxyphenyl)-2-phenyl-1-ethanone | C15H14O2 | 详情 | 详情 | |
| (XXII) | 63437 | 1-(4-methoxyphenyl)-2-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanone | C22H26O4 | 详情 | 详情 | |
| (XXIII) | 17616 | bromo(phenyl)magnesium; Phenyl Magnesium Bromide | 100-58-3 | C6H5BrMg | 详情 | 详情 |